1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-cyclopropyl-1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717333Notes

Reaction equation

HRID 1717333 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][C:5]=1[N:15]1[CH:19]=[C:18]([C:20]([OH:22])=O)[N:17]=[N:16]1)[CH3:2].[CH:23]1([NH2:26])[CH2:25][CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH:23]1([NH:26][C:20]([C:18]2[N:17]=[N:16][N:15]([C:5]3[CH:6]=[CH:7][C:8]([C:10]([NH:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:4]=3[O:3][CH2:1][CH3:2])[CH:19]=2)=[O:22])[CH2:25][CH2:24]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 685156141-[2-ethoxy-4-[(ethylamino)carbonyl]phenyl]-1H-1,2,3-Triazole-4-carboxylic acid

Product 1

HCID 57664951N-cyclopropyl-1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 76%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{2-ethoxy-4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (0.36 g) obtained in Example 131f) in DMF (3 ml) were successively added cyclopropylamine (0.10 ml), triethylamine (0.20 ml), HOBt (0.22 g) and WSC (0.27 g), and the reaction mixture was stirred at room temperature overnight. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol-water to give the title compound as a white powder (0.31 g, 76%).

Workup

  1. customthe organic layer was separated
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-5b565311ddc24002a046127cc40c74e3
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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